A truce on the Smiles rearrangement: revisiting an old reaction--the Truce-Smiles rearrangement.
The Smiles rearrangement is the intramolecular nucleophilic aromatic substitution reaction incorporating a heteroatom as the nucleophilic component and an activated electrophilic arene. One particular variation--the Truce-Smiles rearrangement--utilises a carbon-based nucleophile and an electrophilic arene which does not require additional activation. Such a variation generates a new carbon-carbon bond and the synthetic utility of this relatively under-utilised rearrangement is discussed in this tutorial review.
Snape
Timothy J
TJ
Manchester Interdisciplinary Biocentre, University of Manchester, Manchester, UK. TJSnape@uclan.ac.uk
D000813:Anilides / Q000737:chemistry; D055598:Chemical Phenomena; D008956:Models, Chemical; D015394:Molecular Structure; D013450:Sulfones / Q000737:chemistry*
D000813:Anilides; D013450:Sulfones